Reelected to the state house in 1887, Wiley would go on to serve in the sessions of 1888-89, and 1896-97. The years 1890-1893 saw him serving in the Alabama Senate, a body that he would be reelected to for the session of 1898-1899. In the last named year Wiley was appointed by then President William McKinley as a Lieutenant Colonel in the 5th Reg. U.S. Volunteer Infantry, an outfit that would soon be deployed to Cuba for the Spanish American War. Wiley would also be retained as an adviser to General Leonard Wood, with whom he would help establish a "civil government" in Cuba's Eastern province.

" I see here....men from all sections of the Union who gallantly responded to the call of duty in 1898. I hold a commission in that war from William McKinley, the ideal President of a great country. I treasure that commission as one of my most beloved and personal possessions."